[(1S,2S,4S,5S,6R,10S)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 3754b1d0-3a8b-4c1b-9d7f-3dd14a9c664f
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(1S,2S,4S,5S,6R,10S)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)COC(=O)C=CC5=CC=C(C=C5)O)OC6C(C(C(C(O6)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)COC(=O)/C=C/C5=CC=C(C=C5)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O
• InChI: InChI=1S/C30H38O16/c1-12-19(34)21(36)23(38)28(42-12)44-25-15-8-9-40-27(45-29-24(39)22(37)20(35)16(10-31)43-29)18(15)30(26(25)46-30)11-41-17(33)7-4-13-2-5-14(32)6-3-13/h2-9,12,15-16,18-29,31-32,34-39H,10-11H2,1H3/b7-4+/t12-,15+,16+,18+,19-,20+,21+,22-,23+,24+,25-,26-,27-,28-,29-,30+/m0/s1
• InChI Key: RLSWHCDMMMGSAZ-QIBPMHEQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₆
• Molecular Weight: 654.60 g/mol
• Exact Mass: 654.21598512 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5971	59.71%
Caco-2	-	0.8899	88.99%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6535	65.35%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8032	80.32%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5081	50.81%
P-glycoprotein inhibitior	-	0.5349	53.49%
P-glycoprotein substrate	-	0.5115	51.15%
CYP3A4 substrate	+	0.6880	68.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.9353	93.53%
CYP2C9 inhibition	-	0.8943	89.43%
CYP2C19 inhibition	-	0.8021	80.21%
CYP2D6 inhibition	-	0.9053	90.53%
CYP1A2 inhibition	-	0.8736	87.36%
CYP2C8 inhibition	+	0.6732	67.32%
CYP inhibitory promiscuity	-	0.7103	71.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5310	53.10%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9274	92.74%
Skin irritation	-	0.7718	77.18%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6963	69.63%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.7944	79.44%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7293	72.93%
Acute Oral Toxicity (c)	III	0.4935	49.35%
Estrogen receptor binding	+	0.7678	76.78%
Androgen receptor binding	+	0.6136	61.36%
Thyroid receptor binding	+	0.5283	52.83%
Glucocorticoid receptor binding	+	0.5599	55.99%
Aromatase binding	-	0.4934	49.34%
PPAR gamma	+	0.7026	70.26%
Honey bee toxicity	-	0.6990	69.90%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7612	76.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.18%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.10%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.47%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.22%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.66%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.52%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.59%	96.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.44%	89.67%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.79%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.03%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.22%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.33%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	84.24%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL3194	P02766	Transthyretin	82.46%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.91%	90.00%

Plants that contains it

• Gmelina arborea

Cross-Links

• PubChem: 21635722
• LOTUS: LTS0266640
• wikiData: Q105240498